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Spectroscopic (far or terahertz, mid-infrared and Raman) investigation, thermal analysis and biological activity of piplartine.
- Source :
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Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy [Spectrochim Acta A Mol Biomol Spectrosc] 2017 Sep 05; Vol. 184, pp. 368-381. Date of Electronic Publication: 2017 May 05. - Publication Year :
- 2017
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Abstract
- Research in the field of medicinal plants including Piper species like long pepper (Piper longum L.- Piperaceae) is increasing all over the world due to its use in traditional and Ayurvedic medicine. Piplartine (piperlongumine, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone), a biologically active alkaloid/amide was isolated from the phytochemical investigations of Piper species, as long pepper. This alkaloid has cytotoxic, anti-fungal, anti-diabetic, anti-platelet aggregation, anti-tumoral, anxiolytic, anti-depressant, anti-leishmanial, and genotoxic activities, but, its anticancer property is the most promising and has been widely explored. The main purpose of the work is to present a solid state characterization of PPTN using thermal analysis and vibrational spectroscopy. Quantum mechanical calculations based on the density functional theory was also applied to investigate the molecular conformation and vibrational spectrum, which was compared with experimental results obtained by Raman scattering, far (terahertz) and mid-infrared adsorption spectroscopy. NBO analysis has been performed which predict that most intensive interactions in PPTN are the hyperconjugative interactions between n(1) N6 and π*(O1C7) having delocalization energy of 50.53kcal/mol, Topological parameters have been analyzed using 'AIM' analysis which governs the three bond critical points (BCPs), one di-hydrogen, and four ring critical points (RCPs). MEP surface has been plotted which forecast that the most negative region is associated with the electronegative oxygen atoms (sites for nucleophilic activity). Theoretically, to confirm that the title compound has anti-cancer, anti-diabetic and anti-platelet aggregation activities, it was analyzed by molecular docking interactions with the corresponding target receptors. The obtained values of H-bonding parameters and binding affinity prove that its anti-cancer activity is the more prominent than the other properties.<br /> (Copyright © 2017 Elsevier B.V. All rights reserved.)
- Subjects :
- Biomarkers chemistry
Biomarkers metabolism
Hydrogen Bonding
Molecular Docking Simulation
Proteins chemistry
Proteins metabolism
Spectrum Analysis, Raman
Static Electricity
Terahertz Imaging
Thermodynamics
Thermogravimetry
Vibration
Piperidones analysis
Piperidones chemistry
Piperidones metabolism
Subjects
Details
- Language :
- English
- ISSN :
- 1873-3557
- Volume :
- 184
- Database :
- MEDLINE
- Journal :
- Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy
- Publication Type :
- Academic Journal
- Accession number :
- 28538206
- Full Text :
- https://doi.org/10.1016/j.saa.2017.05.007